data_6 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H10 Br N3 O4 S' _chemical_formula_weight 372.20 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Br' 'Br' -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 'monoclinic' _symmetry_space_group_name_H-M 'P2(1)/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.740(4) _cell_length_b 5.845(3) _cell_length_c 16.093(5) _cell_angle_alpha 90.00 _cell_angle_beta 92.37(2) _cell_angle_gamma 90.00 _cell_volume 1385.3(9) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max .33 _exptl_crystal_size_mid .25 _exptl_crystal_size_min .21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.785 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 3.137 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2692 _diffrn_reflns_av_R_equivalents 0.0525 _diffrn_reflns_av_sigmaI/netI 0.0562 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.38 _diffrn_reflns_theta_max 25.57 _reflns_number_total 2588 _reflns_number_gt 1689 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0594P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0031(8) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2588 _refine_ls_number_parameters 203 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0910 _refine_ls_R_factor_gt 0.0356 _refine_ls_wR_factor_ref 0.0983 _refine_ls_wR_factor_gt 0.0894 _refine_ls_goodness_of_fit_ref 0.962 _refine_ls_restrained_S_all 0.962 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br Br -0.65849(3) -0.39677(7) -0.01179(3) 0.05628(19) Uani 1 1 d . . . S S -0.84888(6) 0.12723(17) 0.11315(5) 0.0401(2) Uani 1 1 d . . . O1 O -0.92681(17) 0.0525(5) 0.06536(15) 0.0551(8) Uani 1 1 d . . . O2 O -0.82505(19) 0.3650(4) 0.11241(15) 0.0501(7) Uani 1 1 d . . . O3 O -0.3442(2) -0.1178(6) 0.1207(3) 0.0858(11) Uani 1 1 d . . . O4 O -0.3679(2) 0.1256(8) 0.2161(2) 0.0876(12) Uani 1 1 d . . . N1 N -0.7661(2) -0.0197(7) 0.0733(2) 0.0472(8) Uani 1 1 d . . . H1 H -0.780(3) -0.115(6) 0.042(2) 0.040(12) Uiso 1 1 d . . . N2 N -0.8978(3) -0.1490(7) 0.4593(2) 0.0540(9) Uani 1 1 d . . . H21 H -0.937(3) -0.245(7) 0.468(2) 0.039(10) Uiso 1 1 d . . . H22 H -0.893(3) -0.037(7) 0.502(3) 0.052(12) Uiso 1 1 d . . . N3 N -0.3943(2) 0.0046(8) 0.1596(2) 0.0610(10) Uani 1 1 d . . . C1 C -0.8583(2) 0.0425(6) 0.2158(2) 0.0328(8) Uani 1 1 d . . . C2 C -0.8958(2) -0.1699(6) 0.2331(2) 0.0413(9) Uani 1 1 d . . . H2 H -0.9114 -0.2701 0.1899 0.050 Uiso 1 1 calc R . . C3 C -0.9098(2) -0.2309(6) 0.3133(2) 0.0415(8) Uani 1 1 d . . . H3 H -0.9355 -0.3723 0.3247 0.050 Uiso 1 1 calc R . . C4 C -0.8858(2) -0.0825(6) 0.3786(2) 0.0363(8) Uani 1 1 d . . . C5 C -0.8476(2) 0.1266(6) 0.3604(2) 0.0412(9) Uani 1 1 d . . . H5 H -0.8315 0.2264 0.4036 0.049 Uiso 1 1 calc R . . C6 C -0.8329(2) 0.1900(6) 0.2795(2) 0.0373(8) Uani 1 1 d . . . H6 H -0.8062 0.3300 0.2680 0.045 Uiso 1 1 calc R . . C7 C -0.6746(2) -0.0113(7) 0.0967(2) 0.0408(9) Uani 1 1 d . . . C8 C -0.6155(2) -0.1712(6) 0.0634(2) 0.0409(9) Uani 1 1 d . . . C9 C -0.5242(3) -0.1654(7) 0.0840(2) 0.0471(10) Uani 1 1 d . . . H9 H -0.4851 -0.2717 0.0617 0.057 Uiso 1 1 calc R . . C10 C -0.4915(3) -0.0012(8) 0.1379(2) 0.0499(10) Uani 1 1 d . . . C11 C -0.5466(3) 0.1611(8) 0.1702(2) 0.0567(11) Uani 1 1 d . . . H11 H -0.5227 0.2738 0.2055 0.068 Uiso 1 1 calc R . . C12 C -0.6385(3) 0.1556(8) 0.1495(2) 0.0542(11) Uani 1 1 d . . . H12 H -0.6766 0.2651 0.1714 0.065 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br 0.0492(3) 0.0484(3) 0.0725(3) -0.0132(2) 0.01746(19) 0.0055(2) S 0.0400(5) 0.0549(6) 0.0256(4) -0.0045(4) 0.0011(3) 0.0173(4) O1 0.0406(14) 0.087(2) 0.0370(14) -0.0203(14) -0.0077(11) 0.0215(14) O2 0.0641(17) 0.0486(16) 0.0382(14) 0.0083(12) 0.0078(12) 0.0181(13) O3 0.0450(17) 0.093(3) 0.119(3) -0.008(2) -0.0001(18) 0.0224(18) O4 0.0544(19) 0.132(3) 0.075(2) -0.010(2) -0.0149(18) -0.001(2) N1 0.0415(17) 0.067(2) 0.0331(18) -0.0156(18) 0.0029(14) 0.0159(17) N2 0.064(2) 0.058(2) 0.040(2) 0.0039(18) 0.0064(17) -0.0260(19) N3 0.045(2) 0.078(3) 0.059(2) 0.012(2) -0.0040(18) 0.007(2) C1 0.0334(17) 0.0379(19) 0.0269(17) -0.0060(14) -0.0021(14) 0.0055(14) C2 0.047(2) 0.041(2) 0.036(2) -0.0186(17) -0.0002(16) -0.0024(16) C3 0.044(2) 0.0346(19) 0.046(2) -0.0017(17) 0.0064(16) -0.0046(16) C4 0.0369(17) 0.044(2) 0.0285(18) 0.0016(16) 0.0034(14) -0.0050(16) C5 0.051(2) 0.042(2) 0.0300(18) -0.0049(17) -0.0008(16) -0.0115(17) C6 0.0416(19) 0.0346(18) 0.036(2) -0.0012(15) 0.0029(15) -0.0025(15) C7 0.0397(19) 0.054(2) 0.0289(18) 0.0049(18) 0.0055(15) 0.0147(18) C8 0.046(2) 0.043(2) 0.033(2) 0.0080(16) 0.0074(16) 0.0117(16) C9 0.045(2) 0.053(2) 0.045(2) 0.0081(19) 0.0115(17) 0.0180(18) C10 0.043(2) 0.067(3) 0.039(2) 0.012(2) -0.0012(17) 0.006(2) C11 0.052(2) 0.080(3) 0.038(2) -0.009(2) 0.0005(18) 0.009(2) C12 0.048(2) 0.072(3) 0.042(2) -0.018(2) -0.0014(18) 0.013(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br C8 1.882(4) . ? S O1 1.424(3) . ? S O2 1.434(3) . ? S N1 1.644(3) . ? S C1 1.736(3) . ? O3 N3 1.220(5) . ? O4 N3 1.203(5) . ? N1 C7 1.386(5) . ? N1 H1 0.78(4) . ? N2 C4 1.374(5) . ? N2 H21 0.83(4) . ? N2 H22 0.95(4) . ? N3 C10 1.461(5) . ? C1 C6 1.379(5) . ? C1 C2 1.392(5) . ? C2 C3 1.364(5) . ? C2 H2 0.9300 . ? C3 C4 1.396(5) . ? C3 H3 0.9300 . ? C4 C5 1.382(5) . ? C5 C6 1.380(5) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C12 1.385(6) . ? C7 C8 1.399(5) . ? C8 C9 1.373(5) . ? C9 C10 1.367(6) . ? C9 H9 0.9300 . ? C10 C11 1.366(6) . ? C11 C12 1.381(6) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 S O2 119.02(17) . . ? O1 S N1 102.97(17) . . ? O2 S N1 108.49(19) . . ? O1 S C1 109.37(17) . . ? O2 S C1 108.30(16) . . ? N1 S C1 108.18(17) . . ? C7 N1 S 127.2(3) . . ? C7 N1 H1 116(3) . . ? S N1 H1 117(3) . . ? C4 N2 H21 118(3) . . ? C4 N2 H22 119(2) . . ? H21 N2 H22 112(3) . . ? O4 N3 O3 123.3(4) . . ? O4 N3 C10 118.5(4) . . ? O3 N3 C10 118.2(4) . . ? C6 C1 C2 120.5(3) . . ? C6 C1 S 119.9(3) . . ? C2 C1 S 119.5(2) . . ? C3 C2 C1 120.0(3) . . ? C3 C2 H2 120.0 . . ? C1 C2 H2 120.0 . . ? C2 C3 C4 120.4(3) . . ? C2 C3 H3 119.8 . . ? C4 C3 H3 119.8 . . ? N2 C4 C5 121.3(3) . . ? N2 C4 C3 119.8(3) . . ? C5 C4 C3 118.9(3) . . ? C6 C5 C4 121.2(3) . . ? C6 C5 H5 119.4 . . ? C4 C5 H5 119.4 . . ? C1 C6 C5 119.0(3) . . ? C1 C6 H6 120.5 . . ? C5 C6 H6 120.5 . . ? C12 C7 N1 122.4(3) . . ? C12 C7 C8 118.4(4) . . ? N1 C7 C8 119.1(4) . . ? C9 C8 C7 120.7(4) . . ? C9 C8 Br 118.2(3) . . ? C7 C8 Br 121.1(3) . . ? C10 C9 C8 119.1(3) . . ? C10 C9 H9 120.4 . . ? C8 C9 H9 120.4 . . ? C11 C10 C9 121.9(4) . . ? C11 C10 N3 119.1(4) . . ? C9 C10 N3 119.0(4) . . ? C10 C11 C12 119.0(4) . . ? C10 C11 H11 120.5 . . ? C12 C11 H11 120.5 . . ? C11 C12 C7 120.8(4) . . ? C11 C12 H12 119.6 . . ? C7 C12 H12 119.6 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 S N1 C7 179.5(4) . . . . ? O2 S N1 C7 52.5(4) . . . . ? C1 S N1 C7 -64.8(4) . . . . ? O1 S C1 C6 -138.9(3) . . . . ? O2 S C1 C6 -7.7(3) . . . . ? N1 S C1 C6 109.7(3) . . . . ? O1 S C1 C2 37.9(3) . . . . ? O2 S C1 C2 169.1(3) . . . . ? N1 S C1 C2 -73.5(3) . . . . ? C6 C1 C2 C3 1.7(5) . . . . ? S C1 C2 C3 -175.1(3) . . . . ? C1 C2 C3 C4 -0.7(5) . . . . ? C2 C3 C4 N2 -178.1(4) . . . . ? C2 C3 C4 C5 -0.1(5) . . . . ? N2 C4 C5 C6 177.8(4) . . . . ? C3 C4 C5 C6 -0.1(5) . . . . ? C2 C1 C6 C5 -1.9(5) . . . . ? S C1 C6 C5 174.9(3) . . . . ? C4 C5 C6 C1 1.1(5) . . . . ? S N1 C7 C12 -11.2(6) . . . . ? S N1 C7 C8 171.4(3) . . . . ? C12 C7 C8 C9 1.3(6) . . . . ? N1 C7 C8 C9 178.8(3) . . . . ? C12 C7 C8 Br -177.8(3) . . . . ? N1 C7 C8 Br -0.3(5) . . . . ? C7 C8 C9 C10 0.2(6) . . . . ? Br C8 C9 C10 179.3(3) . . . . ? C8 C9 C10 C11 -1.8(6) . . . . ? C8 C9 C10 N3 -179.9(3) . . . . ? O4 N3 C10 C11 12.9(6) . . . . ? O3 N3 C10 C11 -168.8(4) . . . . ? O4 N3 C10 C9 -168.9(4) . . . . ? O3 N3 C10 C9 9.5(6) . . . . ? C9 C10 C11 C12 1.8(7) . . . . ? N3 C10 C11 C12 180.0(4) . . . . ? C10 C11 C12 C7 -0.2(7) . . . . ? N1 C7 C12 C11 -178.7(4) . . . . ? C8 C7 C12 C11 -1.3(6) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.57 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.620 _refine_diff_density_min -0.584 _refine_diff_density_rms 0.077